Anthracene derivative and process for making the same



l atented Apr. 21, 1925,

I UNITED STATES PATIENT OFFICE...

BEBHRAM MAYER, or BASEL: AND JAKOB'W'E'IRGLER, or nnunwmnnmn BASEL, SWITZERLAND, ASSIGNOBS T SOCIETY or CHEMICAL INDUSTRY m BASLE, or

' 'nasnt, SWITZERLAND.

ANTHRACENE DERIVATIVE AND PROCESS FOR MAKING THE SAME.

- Switzerland, and the latter at Neuewelt,

near Basel, Switzerland, have invented a new and useful New Anthracene Derivative and Process of Making the Same, of which the following is a full, clear, and exact speci- This invention relates to a new anthracene derivative and to a noveland useful process of making the same.

It has been found that a new anthracene derivative, the anthracene-2-thioglycolio-3- carboxylic acid, is obtained by treating the anthraquinone- 2 -thioglycolic- 3 carboxylic acid With reducing agents.

The anthracene-2-thioglycolic-3-carboxy-,

lie acid, thus obtained, which is of great industrial importance as a starting material for the manufacture of Valuable new dyestuifs and intermediate products, forms a citron-yellow powder. It is sparingly solu- 5 ble in nitrohenzene, alcohol and boiling water, but soluble in boiling glacial acetic acid to a yellowish solution, in sulphuric acid to an orange solution and in ch1orosul-- phonic acid to a solutionwhich is at first aoydeepvred and then brown. In cold alkalies it dlssolves sparingly, but freely in hot alkalies to an olive solution.

It corresponds with 7 great probability to the following formula:

Inerder to illustrate the new process iiiore fully the followingexample' is given, the

parts being byweightw I Applicationfiled January 4, 1924. Serial No. 684,451.

Example.

Y parts of anthraquinone-2-thioglycolic-' 3-carboxylic acid are introduced into 1000' parts ofiammonia of 12 per cent strength, 125 parts of zinc dust are added and the mng'ture is boiled in a reflux apparatus, while stirring well, until the solution which 1s at first deep cherry-red and then brown is completely decolorized. The solution is then filtered from the zinc, the ammonia distilled and the liquid again filtered and treated hot with a mineral acid to produce a precipitate which is a citron-yellow powder consisting of anthracene-2-thioglycolic- 3-carboxylic acid, 1

What we claim is:

'As a new product of manufacture the herein described anthracene-2-thioglycolic-- 3-carboxylic acid having most probably the formula: v

s-cHi-'coon which forms a citron-yellow powder, spar- 1ngly soluble in nitrobenzene, alcohol, andboiling water, but soluble in boiling glacial. acetic acid to a yellowish solution, in sulphuric acid to an orange solution, in chlorosulphonic acid to a solution which is at first deep red and then brown, and in hot alkalies to an olive solution.

In witness whereof we have hereunto 'signed'our names this 20th day of December,

1923, in the presence of two subscribing witnesses. f

a BERTRAM MAYER. JAKOB WURGLER.

Witnesses:' j v Ammo BAUN M. Smemm. 

